Water → HCID 86681865, compound

HRID 1749371Notes

Reaction equation

HRID 1749371 reaction equation
[CH3:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([O:8]C(C2C=CC([N+]([O-])=O)=CC=2)=O)[CH2:4][N:3]1[C:20]([O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:21].[OH-].[Na+].O>C1COCC1.CO>[OH:8][C@H:5]1[CH2:4][N:3]([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[C@H:2]([CH3:1])[CH2:7][CH2:6]1

Participants

6

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86681863HCID 86681863, compound

Product 1

HCID 86681865HCID 86681865, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl (2R,5R)-2-methyl-5-{[(4-nitrophenyl)carbonyl]oxy}piperidine-1-carboxylate (54.3 g, 136 mmol) in THF (850 mL) and MeOH (138 mL) was added 1 N NaOH (204 mL) and water (30 mL). The solution was stirred overnight, then concentrated in vacuo. The residue was diluted with minimal brine and water and extracted twice with EtOAc. The organics were washed with brine, dried over MgSO4, filtered, and concentrated to give the titled compound as a crude, orange-yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.28-7.36 (m, 5H), 5.14 (d, J=3.5 Hz, 2H), 4.50 (t, J=6.8 Hz), 1H), 4.09 (d, J=8.8 Hz, 1H), 3.94 (s, 1H), 3.09 (dd, J=14.3, 1.9 Hz, 1H), 2.06-2.15 (m, 1H), 1.96 (br s, 1H), 1.75-1.83 (m, 1H), 1.66-1.72 (m, 1H), 1.24-1.32 (m, 2H), 1.16 (d, J=7.0 Hz, 2H) ppm. LRMS m/z (M+H) 250.1 found, 250.1 required.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with minimal brine and water
  3. extractionextracted twice with EtOAc
  4. washThe organics were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea5f6faa9818403ebaa2ce0cd74e4543
Source dataset
uspto-grants-2015_10
Patent number
US09156819B2

Reaction notes

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